3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-pyrano[3,2-c]pyridine | 108031-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-pyrano[3,2-c]pyridine
• 英文别名: 2,2-dimethyl-3,4-epoxy-6-azachroman；2,2-dimethyl-3,4-dihydro-3,4-epoxy-2H-pyrano[3,2-c]pyridine；2,2-dimethyl-1a,7b-dihydro-2H-1,3-dioxa-6-aza-cyclo-propa[a]naphthalene；5,5-dimethyl-3,6-dioxa-10-azatricyclo[5.4.0.02,4]undeca-1(7),8,10-triene
• CAS: 108031-10-3
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: XRBMNBBAJQIWMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-pyrano[3,2-c]pyridine 在 potassium tert-butylate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 15.5h， 生成 2,2-dimethyl-4-(2-pyridon-1-yl)-2H-pyrano<3,2-c>pyridine N-oxide
  参考文献：
  名称：

  Relaxant activity of 4-amido-3,4-dihydro-2H-1-benzopyran-3-ols and 4-amido-2H-1-benzopyrans on guinea pig isolated trachealis

  摘要：

  A series of 4-amido-3,4-dihydro-2H-1-benzopyran-3-ols and 4-amido-2H-1-benzopyrans related to the potassium channel activator cromakalim have been prepared and evaluated for their relaxant activity in guinea pig isolated tracheal spirals. Several analogues show enhanced relaxant activity relative to cromakalim in this preparation and the rank order of potency for those substituents investigated at C-6 was CF3 greater than CN greater than C2H5 greater than aza greater than or equal to CH3. One compound, trans-3,4-dihydro-2,2-dimethyl-4-(2-oxopiperidin-1-yl)-7-(trifluor omethyl)-2H- 1-benzopyran-3-ol (24), was resolved into its two enantiomers and the activity was shown to reside essentially in the (+)-isomer, adding further support to the suggestion that the smooth muscle receptor for these potassium channel activators is stereoselective.

  DOI：

  10.1021/jm00173a019
• 作为产物：
  描述：

  2,2-dimethyl-2H-pyrano<3,2-c>pyridine 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-pyrano[3,2-c]pyridine
  参考文献：
  名称：

  Variation in the aromatic ring of cromakalim: antihypertensive activity of pyranopyridines and 6-alkyl-2H-1-benzopyrans

  摘要：

  The synthesis and antihypertensive activity in the spontaneously hypertensive rat of two new series of analogues related to cromakalim (1) are described. In the first series, where the benzopyran nucleus has been replaced by a pyranopyridine nucleus, the position of the nitrogen atom has been found to be critical for activity, and the most potent compounds are the pyrano[3,2-c]pyridines. In the second series, where the powerful electron-withdrawing cyano group of compound 1 has been replaced by alkyl and phenyl groups, the order of antihypertensive potency is ethyl, isopropyl, tert-butyl greater than propyl, cyclopentyl greater than methyl greater than phenyl.

  DOI：

  10.1021/jm00173a018

文献信息

• NOVEL BENZOPYRAN DERIVATIVES AS POTASSIUM CHANNEL OPENERS
  申请人：Zhang Xuqing

  公开号：US20070049556A1

  公开（公告）日：2007-03-01

  The present invention is directed to novel benzopyran derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders related to potassium channel.

  本发明涉及新型苯并吡喃衍生物，含有它们的药物组合物以及它们在治疗与钾通道相关的疾病中的应用。
• Benzopyran derivatives
  申请人：Beecham Group p.l.c.

  公开号：EP0398665A1

  公开（公告）日：1990-11-22

  A compound of formula (I): or, where appropriate, a pharmaceutically acceptable salt, ester or amide thereof, or a pharmaceutically acceptable solvate thereof wherein: X represents O or S; Y represents N or N⁺-O⁻ or a moiety CR₇ wherein R₇ is as defined below; Z represents O, CH₂, NR, S(O)n or Z represents a bond; R represents hydrogen, alkyl or alkylcarbonyl R₁ and R₂ independently represent hydrogen or alkyl; or R₁ and R₂ together represent a C₂₋₇ polymethylene chain; R₃ represents hydrogen, hydroxy, alkoxy or acyloxy; R₄ is hydrogen; R₅ is hydrogen or R₄ and R₅ together represent a bond; R₆ represents hydrogen, substituted or unsubstituted alkyl, alkoxy, C₃₋₈ cycloalkyl, hydroxy, nitro, cyano, halo, formyl, carboxy, a group of formula RaT¹-, RbRcNT-, RaT²NH-, RdCO.O-, RdCS.O-, Rd(OH)CH-, Rd(SH)CH-, RdC(=N.OH)-, RdC(=N.NH₂)- or alkenyl optionally substituted by alkylcarbonyl, nitro or cyano; when Y represents CR₇, R₇ is independently selected from the variables mentioned above in relation to R₆ providing that at least one of R₆ or R₇ is other than hydrogen; Ra represents Rd or RdO- and Rd represents substituted or unsubstituted alkyl, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl, optional substituents for Rd being up to 3 substituents selected from alkyl, alkoxy, hydroxy, halo, haloalkyl, nitro and cyano; Rb and Rc each independently represent hydrogen, alkyl or alkylcarbonyl; T represents a bond or T¹, T¹ represents -CS- or T² and T² represents -CO-, -SO- or -SO₂- and R₈ represents hydrogen, alkyl or substituted or unsubstituted aryl; R₉ represents hydrogen or alkyl, substituted or unsubstituted aryl or R₈ and R₉ together represent a C₃₋₇ polymethylene group; and n represents 0, 1 or 2; a process for preparing such a compound, a pharmaceutical composition containing such a compound and the use of such a compound or composition in medicine.

  化合物的化学式为（I）：或在适当情况下，其药学上可接受的盐，酯或酰胺，或其药学上可接受的溶剂化合物，其中：X代表O或S；Y代表N或N⁺-O⁻或CR₇基团，其中R₇如下所定义；Z代表O，CH₂，NR，S（O）n或Z代表一个键；R代表氢，烷基或烷基羰基；R₁和R₂独立地代表氢或烷基；或R₁和R₂一起代表一个C₂₋₇多亚甲基链；R₃代表氢，羟基，烷氧基或酰氧基；R₄代表氢；R₅代表氢或R₄和R₅一起代表一个键；R₆代表氢，取代或未取代的烷基，烷氧基，C₃₋₈环烷基，羟基，硝基，氰基，卤素，甲酰基，羧基，公式RaT¹-，RbRcNT-，RaT²NH-，RdCO.O-，RdCS.O-，Rd（OH）CH-，Rd（SH）CH-，RdC（=N.OH）-，RdC（=N.NH₂）-或烯基，可选地用烷基羰基，硝基或氰基取代；当Y代表CR₇时，R₇独立地从上述与R₆有关的变量中选择，前提是R₆或R₇中至少有一个不是氢；Ra代表Rd或RdO-，而Rd代表取代或未取代的烷基，取代或未取代的芳基或取代或未取代的杂环基，Rd的可选取代基包括最多3个从烷基，烷氧基，羟基，卤素，卤代烷基，硝基和氰基中选择的取代基；Rb和Rc各自独立地代表氢，烷基或烷基羰基；T代表一个键或T¹，T¹代表-CS-或T²，T²代表-CO-，-SO-或-SO₂-，而R₈代表氢，烷基或取代或未取代的芳基；R₉代表氢或烷基，取代或未取代的芳基或R₈和R₉一起代表一个C₃₋₇多亚甲基基团；n代表0，1或2；制备这种化合物的方法，含有这种化合物的药物组合物以及这种化合物或组合物在医药中的用途。
• Compound and treatment
  申请人：Beecham Group p.l.c.

  公开号：US05254557A1

  公开（公告）日：1993-10-19

  A compound of formula (IA) in the form of a pharmaceutically acceptable microfine powder is disclosed. ##STR1##

  公开了以药用可接受的微细粉末形式的化合物（IA）的化学式。
• Azachroman derivatives with effects on the cardiovascular system
  申请人：Merck Patent Gesellschaft mit beschrankter Haftung

  公开号：US04931454A1

  公开（公告）日：1990-06-05

  An azachroman derivative of the formula ##STR1## wherein Z is (a) --N.dbd.CH--CH.dbd.CH--, (b) --CH.dbd.N--CH.dbd.CH--, (c) --CH.dbd.CH--N.dbd.CH-- or (d) --CH.dbd.CH--CH.dbd.N--; R.sup.1 is A, R.sup.2 is H or A, or R.sup.1 and R.sup.2 together are alkylene with 3-6 C atoms; R.sup.3 is OH or OAc, R.sup.4 is H, or R.sup.3 and R.sup.4 together are a bond; R.sup.5 is 1H-2-pyridon-1-yl, 1H-6-pyridazinon-1-yl, 1H-2-pyrimidinon-1-yl, 1H-6-pyrimidinon-1-yl, 1H-2-pyrazinon-1-yl or 1H-2-thiopyridon-1-yl, or 1H-2-pyridon-1-yl, 1H-6-pyridazinon-1-yl, 1H-2-pyrimidinon-1-yl, 1H-6-pyrimidinon-1-yl, 1H-2-pyrazinon-1-yl or 1H-2-thiopyridon-1-yl mono- or disubstituted by A, F, Cl, Br, I, OH, OA, OAc, NO.sub.2, NH.sub.2, AcNH, HOOC or AOOC; A is C.sub.1-6 -alkyl and Ac is C.sub.1-18 -alkanoyl or C.sub.7-11 -aroyl; or a pharmaceutically acceptable salt thereof is claimed. This compound exhibits vasodilatory and anti-hypertensive effects and is suitable for the treatment of alopecia.

  一种azachroman衍生物，其化学式为##STR1##其中Z为(a) --N.dbd.CH--CH.dbd.CH--, (b) --CH.dbd.N--CH.dbd.CH--, (c) --CH.dbd.CH--N.dbd.CH--或(d) --CH.dbd.CH--CH.dbd.N--; R.sup.1为A，R.sup.2为H或A，或R.sup.1和R.sup.2共同为3-6个碳原子的烷基；R.sup.3为OH或OAc，R.sup.4为H，或R.sup.3和R.sup.4共同为键；R.sup.5为1H-2-吡啶酮-1-基，1H-6-吡啶嗪酮-1-基，1H-2-嘧啶酮-1-基，1H-6-嘧啶酮-1-基，1H-2-吡嗪酮-1-基或1H-2-硫代吡啶酮-1-基，或者1H-2-吡啶酮-1-基，1H-6-吡啶嗪酮-1-基，1H-2-嘧啶酮-1-基，1H-6-嘧啶酮-1-基，1H-2-吡嗪酮-1-基或1H-2-硫代吡啶酮-1-基单取代或双取代的A、F、Cl、Br、I、OH、OA、OAc、NO.sub.2、NH.sub.2、AcNH、HOOC或AOOC；A为C.sub.1-6-烷基，Ac为C.sub.1-18-酰基或C.sub.7-11-芳酰基；或其药学上可接受的盐。该化合物表现出血管扩张和降压作用，并适用于治疗脱发。
• Benzopyran derivatives as potassium channel openers
  申请人：Janssen Pharmaceutica NV

  公开号：US07812183B2

  公开（公告）日：2010-10-12

  The present invention is directed to novel benzopyran derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders related to potassium channel.

  本发明涉及新型苯并吡喃衍生物，包含它们的药物组合物以及它们在治疗与钾通道相关的疾病中的应用。